NBA: SportsLine Projection Model evaluates the trade between the Celtics and Trail Blazers

SportsLine principal data engineer Stephen Oh offers his model's insight on the trade between Boston and Portland

The Boston Celtics have made a cost-cutting decision as they reportedly traded Jrue Holiday to the Portland Trail Blazers for Anfernee Simons and a pair of future second-round draft picks. The deal frees up $4.7 million for the Celtics for the 2025-26 season, but the team also is off the hook for the $72 million Holiday is owed for the following two campaigns and will save an estimated $40 million in luxury taxes.

Boston actually acquired Holiday from Portland on Oct. 1, 2023, four days after the Milwaukee Bucks sent him to the Trail Blazers in a three-team deal that also included the Phoenix Suns. The 35-year-old guard played a big role in the Celtics' march to their 18th NBA championship in 2024, providing leadership and strong defensive play. His scoring dipped with the club, however, as he averaged 12.5 points in 2023-24 and 11.1 last season—his lowest average since his 2009-10 rookie campaign with the Philadelphia 76ers (8.0).

Simons offers more to Boston in terms of offense, as he averaged at least 17.3 points in each of his last four seasons with Portland. The 26-year-old shooting guard, who produced 19.3 points per game in 2024-25, also has shot 38.1% from 3-point range over his seven-year career.

SportsLine principal data engineer Stephen Oh doesn't view the trade as successful in terms of the 2025-26 standings, however. Prior to the deal, Oh's SportsLine Projection Model had the Celtics posting 57.8 victories next season. Now, the model's simulations say the team will finish with 54.1 wins.

 Even though Holiday didn't score as much in 2024-25, Oh can't overlook the fact Boston was better with him in the lineup.

"Despite his lowest career scoring average since his rookie season, the Celtics did have +9.2 point differential (and won 73% of games) with him versus +7.2 (and 69.6% of games won) without him," Oh said. "With Holiday playing, the Celtics averaged nearly +1 more points per game and allowed 1 fewer per game."

In contrast, the Trail Blazers were less successful with Simons than they were without him.

"The sample size is small, but Portland lost 60% of the 70 games in which Simons played last season, losing by an average of 4.4 points while allowing opposing teams to shoot 36.9% from 3-point range," Oh said. "But in the 12 games Simons missed, Portland dominated defensively, allowing just 31.1% shooting from 3-point range. And its eight wins were by an average of 5.4 points."

Oh feels that if you factor in their age and Simons' upside should he become at least an average defender, the trade is not only fair but probably in Boston's favor in the long term. But for 2025-26, he believes it's Portland that gets the better end of the deal.

BOSTON CELTICS	WINS	WIN%	MAKE PLAYOFFS	WIN CONFERENCE	WIN CHAMPIONSHIP
Before trade	57.8	70.5%	99.9%	35.73%	14.14%
After trade	54.1	66.0%	99.9%	24.6%	7.65%
Difference	-3.7	-4.5%	0%	-11.13%	-6.49%

PORTLAND TRAIL BLAZERS	WINS	WIN%	MAKE PLAYOFFS	WIN CONFERENCE	WIN CHAMPIONSHIP
Before trade	39.7	48.4%	20.6%	0.11%	0.04%
After trade	41.4	50.5%	31.8%	0.49%	0.21%
Difference	1.7	2.1%	11.3%	0.38%	0.17%